Acetic Acid → 3,5-Dioxohexanoic acid

HRID 1078794Notes

Reaction equation

HRID 1078794 reaction equation
CN1[CH2:7][CH2:6][O:5]CC1.ClC([O:11][CH2:12][CH:13](C)C)=O.[H][H].[C:18]([OH:21])(=[O:20])[CH3:19]>O1CCCC1.[Pd]>[CH3:13][C:12]([CH2:7][C:6]([CH2:19][C:18]([OH:21])=[O:20])=[O:5])=[O:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 178418361HCID 178418361, compound

Product 1

HCID 54598443,5-Dioxohexanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The fully protected dipeptide formed above was deblocked by treatment with 1/2 trifluoroacetic acid/dichloromethane at room temperature, followed by neutralization with saturated aqueous potassium bicarbonate. Extraction into ethyl acetate and evaporation gave the partially deblocked dipeptide, which was added to a solution prepared from Na -benzyloxycarbonyl glycine, N-methylmorpholine, and isobutyl chloroformate in dry tetrahydrofuran at -15° C. The resulting protected tripeptide was deblocked by treatment with hydrogen in the presence of 10% palladium on carbon in glacial acetic acid. Filtration and lyophilization gave the title compound as its triacetate salt.

Workup

  1. additionwas added to a solution
  2. filtrationFiltration and lyophilization

Sources & evidence

ORD record
ord-ec36bd7d4511429b9d9ff29d3bd4f9d2
Source dataset
uspto-grants-1996_08
Patent number
US05550183

Reaction notes

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